Alex Gibney's The Inventor: Out for Blood is a great movie on Theranos, while General Magic is also solid, about a startup that failed but for very different reasons.
Slidebean's Startup Forensics series is a decent YouTube series on short films about tech startups and larger companies that didn't quite make it- I quite like the look into why Tilt failed:
https://www.youtube.com/channel/UC4bq21IPPbpu0Qrsl7LW0sw
Does anyone have any recommendations?